8uniquechallenges in
enterprise selling

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Imagine a client roster filled with the biggest
and best of the world’s corporations with
names like Apple, IBM, Samsung, General
Motors and Walmart.
Now imagine working with those clients every day, delivering great service and earning the right
to grow your relationships over time.
Winning enterprise business presents unique challenges to selling teams and selling
organizations in general. First, you need to understand how selling to large corporations differs
from the less complex world of selling to small and medium-sized companies. It takes time,
energy, commitment and money but the payoff can be huge.
Here are eight challenges we at Sandler see every day in serving our clients selling into the
enterprise space, and how to overcome them:
8 Unique Challenges in Enterprise Selling

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38 Unique Challenges in Enterprise Selling
The competition is sophisticated
and relentless.
Your competition for enterprise business will be sophisticated, strategically focused and
absolutely relentless. They will come prepared.
The solution: Don’t make the mistake of underestimating them. Understand their who, what,
where, when and how. Research their history, relationships and track record with the account
you’re targeting. Understand not only their business models,
strategies and offerings but the customized value
propositions that they are likely to present in a
specific pursuit. Act on what you learn. It may
drive your Go/No-Go decision about whether
to accelerate a pursuit or exit early.
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FINISH

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48 Unique Challenges in Enterprise Selling
When selling to enterprise clients, prepare to learn patience. The sales cycle can take
months and, in some cases, years.
The solution: Know the buyer network so well at the account you’re targeting, that
you’re informed about its time frames. Have the right people on your pursuit team to
ensure effective and timely solution development. Gain your client’s fingerprints on
how you plan on proceeding every step of the way. Establish
a systematic process for driving Go/No-Go decisions
and use it consistently.
The sales cycle can be lengthy.2.

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8 Unique Challenges in Enterprise Selling 5
The investments can be significant.
Pursuing an enterprise client requires a significant financial commitment as well as
human, managerial and logistical resources. And the opportunity costs connected
with enterprise pursuits can handcuff an organization’s ability to take advantage of
other initiatives.
The solution: Conduct focused territory planning so you
maximize your chances to do what you do best where you’re
most likely to be successful. Profile all of the accounts in your
portfolio so you can customize account planning and map
your resources as relevantly as possible. Use collaborative
account planning to ensure that you go after winnable
accounts. Save resources by reusing assets effectively so
you’re not recreating solutions.
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8 Unique Challenges in Enterprise Selling 6
The buyer networks are wide and diverse.
The buying centers of enterprise clients are comprised of a wide variety of functions that
may include HR, purchasing, accounting, marketing and legal. It can be a little overwhelming
and make you long for the days when you sold to a single buyer across a desk.
The solution: Use your advocates on the inside of the
account to understand how the various functions in its
buyer network collaborate. Understand the impact of
every individual buyer. Expect the
unexpected and be prepared to deal
with new influences over the course
of the long sales cycle because they’ll
surely come.
4.

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8 Unique Challenges in Enterprise Selling
The buyer networks of enterprise clients encompass many functions, and
so should your sales team. Since enterprise organizations buy in teams,
organizations seeking their business must typically sell
in teams as well. Without question, it makes the sale
more complicated but it’s an absolute necessity.
The solution: When it comes to landing an enterprise
client, everybody in the selling organization is on
the selling team. So tap into the expertise of your
coworkers for help in mapping to subject matter
experts at your target accounts. Having corresponding
representatives on your team will show the strength
and substance enterprise clients demand.
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The necessity of a cross-functional
sales team is a given.
5.

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8 Unique Challenges in Enterprise Selling 8
In traditional selling, decisions are typically made quickly and based on price versus
performance. In the enterprise world, however, the decision process can be complex,
multilayered and lengthy.
The solution: Get a clear picture early in the process of the decision structure
and financial models used in the client’s buying decision process. Understand the
requirements of the deal and allow that to drive dynamic Go/No-Go
decisions. Clearly understand an opportunity’s potential rewards
and risks and work to mitigate the risks as a key component of
the pursuit. Your success in this area is critical to the decision
to accelerate or exit.
The decision structures are complex.6.

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8 Unique Challenges in Enterprise Selling 9
Enterprise clients don’t present simple and direct structures to your selling team.
They differ from smaller entities in their complex structures, multiple business
lines, portfolio complexity, depth and breadth of markets served, and
globalization issues.
The solution: Enterprises are marketplaces unto themselves so do
your research to understand the complexities and opportunities they
present. Effective and collaborative account planning combined with
a logical framework of pursuit management will position you to
gain clarity from the complexity.
The organization and its footprint
are incredibly diverse.
7.

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8 Unique Challenges in Enterprise Selling 10
With the enterprise client, the business value of the solutions you develop and
implement must be unassailable or winning their business will be impossible. The pains
and needs of the client, not your product or service, must completely drive the value.
The solution: Build your client intimacy from account planning through service
delivery. Your deep understanding of the pains
driving your customer’s needs earns you the right
to build a customized solution with an integrated
value proposition, highlighting specific and
measured business value over time.
The focus on business value is laser-like.8.

8 Unique Challenges in Enterprise Selling 11
Winning profitable business from enterprise
organizations comes with complications
that make it more challenging than selling to
smaller entities.
The Sandler Enterprise Selling (SES) program can help. With SES, we’ve taken everything that’s made
our training so effective and elevated it to address the needs of organizations selling to enterprise
accounts. The result is a highly strategic system that will help you win business with enterprise clients,
serve them effectively and expand the relationships over time.
Learn more about Sandler Enterprise Selling.
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